The present invention relates to the use of 4-hydroxyisothiazole compounds as antimicrobially active substances, certain new 4-hydroxyisothiazole compounds and a process for their preparation.
It is known that certain halogenated 3-hydroxyisothiazole compounds have an excellent antimicrobial activity, as disclosed in U.S. Pat. No. 3,887,352. However it is desirable to be able to provide non-halogenated agents which are highly effective antimicrobial agents. Polymeric materials can be antimicrobially finished by incorporating halogenated compounds, the active substances being, as a result of their excellent migration properties, constantly conveyed to the surface of the corresponding material (xe2x80x9cslow releasexe2x80x9d). For certain industrial applications, this effect is undesired since the long-term effect of antimicrobially finished materials such as textiles, paper, plastics, cellulose sponges etc. is reduced at the same time.
The object of the present invention is thus to provide non-halogenated 4-hydroxyisothiazole compounds for use as antimicrobially active substances and which, at the same time, are stable to migration.
The present invention provides the use of 4-hydroxyisothiazole compounds of the following formulae 
R1 and R2 are independently of each other hydrogen; C1-C10 alkyl; substituted C1-C10alkyl; C1-C10acyl; substituted C1-C10acyl; C6-C10aryl; substituted C6-C10aryl; C6-C10aryl carbonyl; or substituted C6-C10arylcarbonyl; as antimicrobial agents.
Of particular interest are compounds of formula (1) as an antimicrobial wherein R1 and R2 are both C6-C10aryl.
A preferred compound is of formula (1) wherein R1 and R2 are both phenyl.
A preferred compound is of formula (2) wherein R2 is C6-C10aryl or substituted C6-C10aryl.
Another aspect of the invention are certain compounds described by formula (1) and (2) which are novel. These novel compounds include compounds of formula 
R1 and R2 are independently of each other hydrogen; C1-C10alkyl; substituted C1-C10alkyl; C1-C1acyl; substituted C1-C10acyl; C6-C10aryl; substituted C6-C10aryl; C6-C10aryl carbonyl; or substituted C6-C10aryl carbonyl.
C1-C10 alkyl may be branched or unbranched such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, n-nonyl, n-decyl.
C6-C10 aryl may be phenyl or naphtyl.
The substituted C1-C10 alkyl, substituted C6-C10 aryl and substituted C6-C10 arylcarbonyl may be substituted by halogen, preferably fluoro, C1-C10 alkoxy or C1-C6 alkyl carbonyl.
C1-C10 alkoxy is straight-chain or branched alkoxy radicals such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, pentyloxy, iso-pentyloxy, tertpentyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy or decyloxy.
C1-C6 alkyl carbonyl is straight-chain or branched carbonyl radicals such as acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl or pivaloyl.
Another aspect of the present invention is a process for the preparation of compounds of formula (1). The process comprises reacting acetic anhydride with an acetic acid substituted on the alpha carbon by R1 or R2, at a temperature of 120xc2x0 C. to 180xc2x0 C., preferably at a temperature of 140xc2x0 C. to 160xc2x0 C. The reaction scheme below shows the reaction, wherein R4 represents R1 or R2 as previously defined. 
The resulting ketone is then stirred with hydroxylamine hydrochloride to produce an oxime: 
The oxime is then stirred with tosyl chloride in an aromatic solvent, such as pyridine, at a temperature of xe2x88x925xc2x0 C. to 5xc2x0 C., preferably at a temperature of xe2x88x922xc2x0 C. to 2xc2x0 C. 
The tosylate is then dissolved in an ether solvent, such as tetrahydrofuran, and added to a cooled solution of potassium metal in dry alcohol, such as ethanol: 
The aminoketone is then heated with thionyl chloride at a temperature of 40xc2x0 C. to 60xc2x0 C., preferably at a temperature of 45xc2x0 C. to 55xc2x0 C.: 
Preferably R4 is phenyl.
Alternatively, by the reaction steps I-IV as shown in the reaction scheme below natural amino acids are obtainable which can be reacted to amino ketones in a Dakin-West reaction (step V). Compounds of formula (2) are formed as by-products: 
The experimental procedure for step I to step IV is elaborated for substrates with R=p-Fluoro substituted compounds and a general procedure is given for the remaining steps (Step V to Step VII).
Step-I:
aluminium chloride 80 g (0.6 mol) is added To a solution of ethyl oxalyl chloride 82 g (0.6 mol) in 200 ml of dichloromethane with stirring at temperature 25-30xc2x0 C. over a period of 30 minutes in portions. Fluorobenzene 48 g (0.5 mol) in 200 ml of dichloromethane is added through a dropping funnel over a period of 2.5 h, maintaining the temperature at 25-30xc2x0 C. Stirring is continued at the same temperature for additional 3 h. Reaction mass is then quenched over 1 l ice-cold water containing 200 ml of HClconc. The organic layer is separated, passed over celite bed and dried over anhydrous Na2SO4. Dichloromethane is distilled off under reduced pressure to get 83 g (84%) of the ketone.
Step-II:
Hydroxylamine hydrochloride (12.25 g, 0.1 76 mol) is added under stirring at room temperature to a solution of the ketone (30 g, 0.153 mol) in 150 ml ethanol. Pyridine (14 ml, 0.18 mol) is added to the stirred reaction mixture and is refluxed for 2.5 h. Pyridine and ethanol are distilled off under reduced pressure. The residue is dissolved in 250 ml of ether and washed with water (200 ml). Ether extract is dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the 32 g (99%) of oxime as a mixture of syn and anti isomers.
Step-III:
2 g of 10 % Pd-C is added to a solution of oxime (20 g, 0.095 mol) in ethanol (300 ml) and acetic acid (25 ml), taken in a 1 l autoclave. Hydrogen is charged into the autoclave till a pressure of 100 psi. The mixture is stirred at 50xc2x0 C. for 5 h. The catalyst is filtered off and the filtrate is concentrated to get brown coloured sticky solid. This residue is taken in dry ether and dry HCl gas passed through it to get white crystalline amine hydrochloride (15.86 g, 72%). 3.2 g (16%) of the staring material is also recovered from ether layer.
Step-IV:
13 g (0.055mol) of the xcex1-amino ester hydrochloride is hydrolysed by refluxing it in 1:1 conc. HCl (60 ml) for 4 h. Reaction mass is cooled to room temperature and pH is adjusted to xcx9c7 to precipitate the free xcex1-amino acid (9 g, 95%).
Step V:
In a typical procedure, a mixture of xcex1-amino acid (47.3 mmol), pyridine (25 ml) and acid anhydride (0.284 mol) is refluxed for 5 h. Pyridine and excess acid anhydride are distilled off under reduced pressure. The residue is purified by column chromatography over silica to get pure a-amidoketone (81%).
Step VI:
In a typical procedure, the a-amidoketone (38.4 mmol) is refluxed with 15% conc HCl (100 ml) for 4 h. The reaction mixture is concentrated to dryness and titurated with 25 ml ethyl acetate to get xcex1-ketoamine hydrochloride as a white crystalline solid (82%).
Step VII:
There are two different procedures which are followed for the conversion of the xcex1-ketoamine hydrochloride to 4-hydroxy isothiazole. Procedure 1 is followed for xcex1-acetoamine hydrochloride (Bull. Chem. Soc. jpn. 41, 1968, 959-964) and procedure 2 is employed for higher homologous a-ketoamine hydrochlorides.
Procedure 1:
To anhydrous DMF (10 ml/1 g of xcex1-ketoamine hydrochloride), maintained at 0xc2x0 C., is added dropwise thionyl chloride (12.5 mmol, 2.5 equivalents). After a lapse of 15 min, to this stirred solution is added xcex1-ketoamine hydrochloride (5 mmol, 1 equivalent) at once. The reaction mixture is stirred at the same temperature for 2 h and then at room temperature for 2 h. The mixture is then poured on ice cold water (50 ml) and extracted with ether (3xc3x9750 ml). The organic layer is washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The dark gummy residue is purified by column chromatography over silica gel to get 4-hydroxy isothiazole monomer and dimer in 12-28% yield.
Procedure 2:
Thionyl chloride (7 equivalents) is added dropwise to chloroform (20 ml/1 g of xcex1-ketoamine hydrochloride) and maintained at 5xc2x0 C. After a lapse of 15 min xcex1-ketoamine hydrochloride (5 mmol, 1 equivalent) is added at once to the stirred solution. The reaction mixture is stirred at the same temperature for 2 h, then refluxed for 2 h. The mixture is then poured on ice cold water (100 ml) and extracted with dichloromethane (3xc3x9750 ml). The organic layer is washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue is purified by column chromatography over silica gel to get 4-hydroxy isothiazole monomer in 48-63% yield.
5-arylcarbonyl-4-hydroxyisothiazoles are obtainable by the following reaction route: 
Pyridine (87 mmol, 31 equivalents) is added to a mixture of ethyl carbamate (22 mmol, 8 equivalents), thionyl chloride (22 mmol, 8 equivalents) in 30 ml of xylene. The mixture is stirred at room temperature for 30 min. Furan derivative (2.8 mmol, 1 equivalent) is added and the mixture is refluxed for 5 h. It is then poured in ice cold water (200 ml) and extracted with ethyl acetate (2xc3x9750 ml). The organic layer is washed with 2% NaHCO3, water; dried over Na2SO4 and concentrated under reduced pressure. The residue is column chromatographed over silica gel to isolate 4-hydroxy isothiazole in 40-50%.
The 4-hydroxyisothiazole compounds according to the invention are thermally stable and antimicrobially effective compounds of low volatility and having a severely reduced tendency to migrate. They are therefore suitable for the antimicrobial finishing of polymeric compounds, for example in plastics, rubbers, paints, surface coatings, (textile) fibres which are exposed to a microbially contaminated environment.
Examples of polymers and other substrates which can be antimicrobially finished in this way are:
polymers of mono- and diolefins,
polyolefins,
copolymers of mono- and diolefins with one another or with other vinyl monomers,
hydrocarbon resins,
polystyrene,
copolymers of styrene or xcex1-methylstyrene or dienes or acrylic derivatives,
graft copolymers of styrene or xcex1-methylstyrene.
halogen-containing polymers,
polymers derived from xcex1,xcex2-unsaturated acids and derivatives thereof, such as polyacrylates and polymethacrylates,
polymers derived from unsaturated alcohols and amines or acyl derivatives or acetals thereof,
homo- and copolymers of cyclic ethers, polyacetals, polyphenylene oxides and polyphenylene sulfides and mixtures thereof with styrene polymers or polyamides,
polyurethanes derived from polyethers, polyesters and polybutadienes having terminal hydroxyl groups on the one hand and aliphatic or aromatic polyisocyanates on the other, and precursors thereof,
polyamides and copolyamides derived from diamines and dicarboxylic acids and/or from aminocarboxylic acids or the corresponding lactams,
polyureas, polyimides, polyamide-imides, polyetherimides, polyesterimides, polyhydantoins and polybenzimidazoles,
polyesters,
polycarbonates and polyester carbonates,
polysulfones, polyether sulfones and polyether ketones,
crosslinked polymers derived from aldehydes on the one hand and phenols, urea or melamine on the other hand, such as phenol-formaldehyde resins, urea-formaldehyde resins and melamine-formaldehyde resins,
drying and non-drying alkyd resins,
unsaturated polyester resins,
crosslinkable acrylic resins,
alkyd resins, polyester resins and acrylate resins,
crosslinked epoxy resins,
superabsorbent polymers
natural polymers, such as cellulose, natural rubber, gelatine, and derivatives thereof modified chemically in a polymer-homologous manner, such as cellulose acetates, cellulose propionates cellulose butyrates, or the cellulose ethers, such as methylcellulose; and also rosins and derivatives.
The invention thus also provides a composition comprising
(A) an organic material to be antimicrobially finished and
(B) at least one compound of the formula (1) or formula (2).
The invention also relates to a process for the antimicrobial finishing of an organic material, which comprises adding at least one compound of the formula (1) or formula (2) thereto, and to the use of the compound of the formula (1) or formula (2) for the antimicrobial finishing of polymeric materials.
The amount of antimicrobial active substance to be used depends on the organic material to be antimicrobially finished and on the intended use of the material finished in this way. The composition according to the invention generally comprises, per 100 parts by weight of component (A), from 0.01 to 15 parts by weight, in particular from 0.05 to 10 parts by weight, and especially from 0.1 to 5 parts by weight of the antimicrobial active substance (component (B)).
The antimicrobial active substance (component (B)) can also be a mixture of two or more compounds of the formula (1) or formula (2). The compositions according to the invention can, in addition to the compounds according to the invention, also comprise other additives, for example antioxidants or light protection agents.
Incorporation into the organic polymers, for example into the synthetic organic, in particular thermoplastic, polymers can take place by adding the 4-hydroxyisothiazole compound according to the invention and, if desired, other additives by the methods customary in the art. Incorporation can expediently take place before or during shaping, for example by mixing the pulverulent components or by adding the antimicrobial active substance to the melt or solution of the polymer, or by applying the dissolved or dispersed compounds to the polymer, if desired with subsequent evaporation of the solvent. Another method of incorporating the mixtures according to the invention into polymers involves adding the former before or during polymerization of the corresponding monomers or before crosslinking.
The mixtures according to the invention can also be added to the organic polymers to be finished in the form of a masterbatch which comprises these compounds, for example, in a concentration of from 2.5 to 25% by weight.
The resulting antimicrobially finished polymer compositions can be converted into shaped articles, for example fibres, films, tapes, sheets, multi-wall sheets, containers, tubes and other profiles, by conventional methods, for example by hot pressing, spinning, extrusion or injection moulding.
The 4-hydroxyisothiazole compounds of the formula (1) or formula (2) are also suitable for the antimicrobial finishing of undyed and dyed or printed fibre materials made, for example, of silk, wool, polyamide, polyester or polyurethane, and in particular of cellulosic fibre materials of all types. Examples of such fibre materials are the natural cellulose fibres, such as cotton, linen, jute and hemp, and also pulp and regenerated cellulose. The 4-hydroxy-isothiazole compounds according to the invention are also suitable for the antimicrobial finishing of hydroxyl-group-containing fibres which are present in mixed fabrics, for example, of mixtures of cotton with polyester fibres or polyamide fibres. The 4-hydroxy-isothiazole compounds of the formula (1) or formula (2) are also suitable for incorporation into non-wovens.
xe2x80x9cNon-wovenxe2x80x9d is a type of fabric that is not spun and woven into a cloth, but instead bonded together. According to the ISO definition it is a manufactured sheet, web, or batt of directionally or randomly orientated fibres, bonded by friction, and/or adhesion.
Nonwoven textiles are widely used in disposable as well as durable goods, such as baby diaper, feminine hygiene, adult incontinence, wipers, bed linings, automotive industries, medical face masks, air and water filtration, home furnishing and geotextiles. Such materials can be fabricated by different techniques, such as spunbonding, melt blown, carded thermal bonding and carded chemical bonding, dry and/or wet laid and needlefelts. Because of the nature of such applications, increasingly the market is demanding products with specific properties such as antimicrobial efficacy.
For this purpose, one or more compounds of the formula (1) or formula (2) are advantageously applied to the textile fibre material in an amount of from 0.01 to 20% by weight, preferably 0.1-3% by weight, and in particular from 0.25 to 2% by weight, based on the weight of the fibre material, in a process analogous to dyeing.
The 4-hydroxyisothiazole compounds according to the invention can be applied to the fibre material and fixed to the fibre in different ways, in particular in the form of aqueous dispersions or printing pastes.
The textile fibre materials finished using the compounds of the formula (1) or formula (2) according to the invention have an excellent and long-lasting antimicrobial protection.
An antimicrobial textile treatment formulation has, for example, the following composition:
20% by weight of a compound of formula (1) or formula (2),
5% by weight of sodium lauryl sulfate,
10 % by weight of an ethoxylated fatty alcohol,
40% by weight of propylene glycol and
25% by weight of water.
The 4-hydroxyisothiazole compounds according to the invention can also be used in paper finishing, printing thickeners containing starch, varnishes and paints.
The 4-hydroxyisothiazole compounds according to the invention are also useful for the disinfection and general antimicrobial treatment, such as deodorising, of the skin, mucous membrane and hair, preferably for the disinfection of hands and wounds.
Therefore, these compounds are suitable as an antimicrobial active substance in personal care products as shampoos, bath- and shower additives, hair-care products, liquid and bar soaps, lotions and cremes, deodorants, other aqueous or alcoholic solutions, for example cleaning solutions for the skin, moist cleaning sheets, oils and powders.
A further subject of the present invention is therefore a personal care composition comprising at least one compound of the formula (1) or formula (2) and cosmetically tolerable carriers or auxiliaries.
The personal care composition according to the present invention comprises 0.01 to 15, preferably 0.5 to 10 % b.w. of the 4-hydroxyisothiazole compounds of formula (1) or formula (2) and cosmetically tolerable carriers or auxiliaries.
The personal care composition according to the invention can be formulated as a water-in-oil or oil-in-water emulsion, as an oil-in-alcohol lotion, as a vesicular dispersion of an ionic or non-ionic amphiphilic lipid, as a gel, solid stick, aerosol formulation or a surfactant based formulation, such as a soap or skin cleanser.
As a water-in-oil or oil-in-water emulsion, the cosmetically compatible auxiliary preferably contains 5 to 50% of an oil phase, 5 to 20% of an emulsifier and 30 to 90% of water. The oil phase can in this case contain any oil suitable for cosmetic formulations, e.g. one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol. Preferred mono- or polyols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerol and sorbitol.
Any conventionally usable emulsifier can be used for the cosmetic composition according to the invention, for example one or more ethoxylated esters of natural derivatives, e.g. polyethoxylated esters of hydrogenated castor oil; or a silicone oil emulsifier, e.g. a silicone polyol; an optionally ethoxylated fatty acid soap; an ethoxylated fatty alcohol; an optionally ethoxylated sorbitan ester; an ethoxylated fatty acid; or an ethoxylated glyceride.
The cosmetic composition may also comprise further components, e.g. emollients, emulsion stabilisers, skin humectants, skin tanning accelerators, thickeners, such as xanthan, moisture-retention agents, such as glycerol, preservatives, perfumes and colourings.
The preparation of the cosmetic composition can be effected by physically mixing the antimicrobial(s) with the auxiliary by customary methods, for example by simply stirring the individual components together.
Cosmetic formulations include a very wide range of cosmetic products. Suitable products are, for example, especially the following:
skin-care products, for example skin washing and cleansing products in the form of bars of soap or liquid soaps, syndets or washing pastes, skin emulsions, multiple emulsions or skin oils;
bath products, for example liquid (foam baths, milks, shower products) or solid bath products, such as bath pearls and bath salts;
decorative body-care products, for example face make-ups in the form of day or powder creams, face powders (lose and compressed), rouge or cream make-ups, eye-care products, for example eye shadow products, mascara, eyeliners, eye creams or eye-fix creams; lip-care products, for example lipstick, lip gloss, lip liner, nail-care products, such as nail varnish, nail varnish remover, nail hardeners or cuticle removers;
feminine hygiene products, such as feminine hygiene washing lotions or sprays;
foot-care products, for example foot baths, foot powders, food creams or foot balms, special deodorants and antiperspirants or products for scrubbing off callouses;
sunscreens, such as sun milks, lotions, creams, oils, sunblockers or tropicals, pre-sun products or after-sun products;
suntanning products, for example self-tanning creams;
depigmenting products, for example products for bleaching or lightening skin;
insect repellents, for example insect oils, lotions, sprays or sticks;
deodorants, for example deodorant sprays, non-aerosol sprays, deodorant gels, sticks or roll-ons;
antiperspirants, for example antiperspirant sticks, creams or roll-ons;
products for cleansing and treating impure skin, for example syndets (solid or liquid), peeling or scrubbing products or peeling masks;
chemical depilatory products, for example depilatory powders, liquid depilatory products, creamy or pasty depilatory products, depilatory gels or aerosol foams;
shaving products, for example shaving soap, foaming shaving creams, non-foaming shaving creams, shaving foams and gels, preshaving products for dry shaving, after-shaves or aftershave lotions;
scents, for example perfumes (Eau de Cologne, Eau de Toilette, Eau de Parfum, Parfum de Toilette, perfume), perfume oils or perfume creams;
products for oral and dental hygiene as well as for dentures, for example toothpastes, tooth gels, tooth powders, mouth-wash concentrates, anti-plaque mouth-washes, denture cleaning products or denture adhesion products;
cosmetic formulations for hair treatment, for example hair washes in the form of shampoos, hair conditioners, hair-care products, for example pretreatment products, hair tonics, hair styling creams and gels, pomades, hair rinses, deep conditioning treatments, intensive hair care treatments, hair setting products, for example waving agents for perms (hot wave, mild wave, cold wave), hair straightening products, liquid hair fixatives, hair foams, hair sprays, bleaching agents, for example hydrogen peroxide solutions, bleaching shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semitemporary or permanent hair dyes, products containing self-oxidising dyes, or natural hair dyes, such as henna or camomile.
An antimicrobial soap has, for example, the following composition:
0.01 to 5% by weight of a compound of the formula (1) or formula (2),
0.3 to 1% by weight of titanium dioxide,
1 to 10 % by weight of stearic acid,
to 100% of soap base, for example the sodium salts of tallow fatty and coconut fatty acid or glycerols.
A shampoo has, for example, the following composition:
0.01 to 5% by weight of a compound of the formula (1) or formula (2),
12.0% by weight of sodium laureth-2-sulfate,
4.0% by weight of cocamidopropylbetaine,
3.0% by weight of NaCl and water to 100%.
A deodorant has, for example, the following composition:
0.01 to 5% by weight of a compound of the formula (1) or formula (2),
60% by weight of ethanol,
0.3% by weight of perfume oil and water to 100%.
The personal care formulations listed above can be in a very wide range of forms of presentation, for example
in the form of liquid formulations as an O/W emulsion,
in the form of a gel,
in the form of an oil, cream, milk or lotion,
in the form of a powder, lacquer, pellets or make-up,
in the form of a stick,
in the form of a spray (spray with propellant or pumping spray).or an aerosol,
in the form of a foam, or
in the form of a paste.
The 4-hydroxyisothiazole compounds according to the invention are useful for the preservation of cosmetic and household products against microbial spoilage.
The oral hygiene composition may comprise an additional antibacterial enhancing agent, for example an anionic polymeric polycarboxylate, a dehydrated polyphosphate salt, a compound which provides a source of fluoride ions, a polishing material, including siliceous material or sodium bicarbonate, an orally acceptable vehicle, including a water-phase with humectant, thickeners, surface-active agents and a flavoring or sweetening material.
The oral hygiene composition according to the invention contains from 0.003 to 5% by weight based on the total weight of the composition, of antimicrobial or a mixture of antimicrobials of the formula (1) or formula (2).
The preparation of the oral hygiene composition can be effected by physically mixing the antimicrobial(s) with the other ingredients by customary methods, for example by simply stirring the individual components together, then mixing further under vacuum.
An oral care formulation has, for example, the following composition:
10 % by weight of sorbitol,
10 % by weight of glycerin,
15% by weight of ethanol,
15% by weight of propylene gylcol,
0.5% by weight of sodium lauryl sulfate,
0.25% by weight of sodium methyl cocyl taurate,
0.25% by weight of poloxypropylene/polyoxyethylene block copolymer,
0.10% by weight of mint flavor,
0.3% by weight of a compound of formula (1) or formula (2),
48.6% by weight of water.
The oral hygiene composition may be in various forms of presentation including the form of a gel, paste, cream or mouthwash.
Furthermore the 4-hydroxyisothiazole compounds according to the invention are useful as household cleaners for the cleaning and disinfection of hard surfaces.
A detergent has, for example, the following composition:
0.01 to 5% by weight of a compound of the formula (1) or formula (2)
3.0% by weight of octanol 4EO,
1.3% by weight fatty alcohol C8-C10-polyglucoside,
3.0% by weight isopropanol,
water to 100%.